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| Title: | Metal-free cyclocarboamination of ortho-formyl phenylacetylenes with secondary amines : access to 1,3-diamino-1H-indenes and 3-amino-1-indanones | Authors: | Cui, JF Tang, R Yang, B Lai, NCH Jiang, JJ Deng, JR Wong, MK |
Issue Date: | 1-Feb-2019 | Source: | Advanced synthesis & catalysis, 1 Feb. 2019, v. 361, no. 3, p. 569-577 | Abstract: | This work first discloses a new strategy for amine activation to give reactive amine anion by in situ generated iminium cation-amine anion pair through decomposition of sterically hindered aminals. Utilizing this strategy, a highly regio- and chemoselective cyclocarboamination of ortho-formyl phenylacetylenes with secondary amines has been realized under metal-free mild reaction conditions. The cyclocarboamination with notably tunable product profiles depends on the separation and purification procedure, a diverse range of 1, 3-diamino-1H-indenes (essentially reactive enamines) and 3-amino-1-indanones were obtained, respectively. Moreover, using iodine as an electrophile to couple with various ortho-formyl phenylacetylenes and secondary amines, a series of 3-amino-2-iodo-1-indanones were efficiently achieved with four bonds (C=O, C−C, C−N and C−I) formation in an one-pot three-component reaction. These results demonstrated an unprecedented methodology for the construction of highly functionalized 1H-indene and 1-indanone compounds. (Figure presented.). | Keywords: | Aminal Amine activation Carboamination Indanone Indene |
Publisher: | Wiley-VCH | Journal: | Advanced synthesis & catalysis | ISSN: | 1615-4150 | EISSN: | 1615-4169 | DOI: | 10.1002/adsc.201801318 | Rights: | © 2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim This is the peer reviewed version of the following article: Cui, J. F., Tang, R., Yang, B., Lai, N. C. H., Jiang, J. J., Deng, J. R., & Wong, M. K. (2019). Metal‐free cyclocarboamination of ortho‐formyl phenylacetylenes with secondary amines: Access to 1, 3‐diamino‐1H‐indenes and 3‐amino‐1‐indanones. Advanced Synthesis & Catalysis, 361(3), 569-577, which has been published in final form at https://doi.org/10.1002/adsc.201801318. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. |
| Appears in Collections: | Journal/Magazine Article |
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